Potassium Hydroxide → HCID 59966108, compound

HRID 651709Notes

Reaction equation

HRID 651709 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13](C#N)[S:14]([N:17]([CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:11]=2)[C:6]([CH2:34][C@H:35]2[CH2:39][CH2:38][CH2:37][N:36]2[CH3:40])=[CH:5]1)[CH:2]=[CH2:3].[OH-].[K+]>C(O)C>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][S:14]([N:17]([CH:19]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:18])(=[O:15])=[O:16])=[CH:10][CH:11]=2)[C:6]([CH2:34][C@H:35]2[CH2:39][CH2:38][CH2:37][N:36]2[CH3:40])=[CH:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53817166HCID 53817166, compound

Product 1

HCID 59966108HCID 59966108, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-[(R)-1-allyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-diphenylmethyl-N-methylmethanesulfonamide (from step (b), 5.11 g, 9.25 mmol) in ethanol (10.22 ml) at ambient temperature was added 2N potassium hydroxide solution (20.4 ml, 41 mmmol). The dark brown solution was then brought to reflux and maintained at this temperature for 15 hr. The oily reaction mixture was then cooled to ambient temperature and extracted with ethyl acetate (3×50 ml). The organic extracts were combined and evaporated in vacuo to yield a dark brown oil. This was purified by flash column chromatography (ethyl acetate:hexane:diethylamine 1:1:0.1 as eluant) to yield the title compound (3.7 g, 76%) as a brown oil.

Workup

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customevaporated in vacuo
  5. customto yield a dark brown oil
  6. customThis was purified by flash column chromatography (ethyl acetate:hexane:diethylamine 1:1:0.1 as eluant)

Sources & evidence

ORD record
ord-1392c3e947bd491d9975f3a217ee31f5
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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